The Alistair Blog
Stories about the broken world of traditional financial advice, deep dives into our microtools, and updates on what we're building to fix it.
The Accuracy Problem in AI Financial Advice
Most AI tools answer financial questions by hoping the model's training data is recent enough. That's a recipe for disaster. Here's what we built instead.
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How Much International Exposure Do You Actually Need?Investing
Bogle said zero. Vanguard says 40%. Academics say market-cap weight at roughly 40%. The US has outperformed for 15 years straight. Is the diversification still worth it?
Dividend Investing: Free Money or the Biggest Illusion in Finance?Investing
Getting paid to own stocks sounds great. But every dollar paid as a dividend is a dollar the company can't reinvest. The academic case against dividend-focused strategies.
Factor Investing for Normal People: Smart Beta or Marketing Gimmick?Investing
The academics discovered factors that beat the market. Wall Street turned them into expensive products. Can retail investors actually capture factor premiums — or is this just the new active management?
Alternative Assets Are No Longer Just for the RichInvesting
Private equity, private credit, interval funds, REITs — asset classes once reserved for institutions and the ultra-wealthy are now accessible through ETFs and platforms. Should you add them?
Why Your Portfolio Underperforms the Market (It's Not Fees)Investing
The average investor underperforms the funds they own by 2-3% per year. Not because of expense ratios. Because they buy high, sell low, and can't stop tinkering.
What the S&P 500 Doesn't Tell You About the EconomyInvesting
The S&P 500 isn't the economy. It's 500 of the largest public US companies, heavily concentrated in tech, and increasingly disconnected from what's actually happening on Main Street.
Cash Stuffing and #FinTok: Are Social Media Budgeting Trends Actually Legit?Money Basics
TikTok has turned personal finance into content. Cash stuffing, no-spend challenges, and loud budgeting are everywhere. Which ones are real strategies and which are just entertainment?
The Case for Never RebalancingInvesting
Every advisor tells you to rebalance annually. But letting your winners ride — never selling, never trimming — actually produces higher long-term returns. Here's the contrarian case.
Sequence of Return Risk: The Retirement Killer Nobody Plans ForRetirement
You can retire with a million dollars, average 8% returns over 30 years, and still run out of money. It all depends on what happens in the first five years. Here's why — and how to protect yourself.
Should You Pay Off Your Mortgage Before You Retire?Retirement
The math says no — a 3% mortgage is cheap leverage. But retirement isn't about maximizing net worth. It's about sleeping at night. The answer depends on more than interest rates.
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